High-yield total synthesis of (-)-strictinin through intramolecular coupling of gallates

Journal of Organic Chemistry

Volumn 78, Issue 9, 2013, Pages 4319-4328

  Michihata, Naoki ^a   Kaneko, Yuki ^a   Kasai, Yusuke ^a,b   Tanigawa, Kotaro ^a   Hirokane, Tsukasa ^a   Higasa, Sho ^a   Yamada, Hidetoshi ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

ARYL-ARYL COUPLING; AXIAL CHIRALITY; INTRAMOLECULAR COUPLING; PERFECT CONTROLS; QUANTITATIVE FORMATION; REACTION CONDITIONS; TOTAL EFFICIENCY; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ELLAGITANNIN; GALLIC ACID; GLUCOSE DERIVATIVE; PHENOL DERIVATIVE; STRICTININ;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR DYNAMICS; OXIDATION; QUANTITATIVE ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; STEREOISOMERISM; VASCULAR PLANT;

CHEMISTRY TECHNIQUES, SYNTHETIC; GALLIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENOLS; PLANT LEAVES; STEREOISOMERISM; TRACHEOBIONTA;

EID: 84877135642     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4003135     Document Type: Article

References (105)

1. Okuda, T.; Yoshida, T.; Ashida, M.; Yazaki, K. Chem. Pharm. Bull. 1982, 30, 766-769
2. Okuda, T.; Yoshida, T.; Ashida, M.; Yazaki, K. J. Chem. Soc., Perkin Trans. 1 1983, 1765-1772
3. Balanophoraceae: Jiang, Z.-H.; Hirose, Y.; Iwata, H.; Sakamoto, S.; Tanaka, T.; Kouno, I. Chem. Pharm. Bull. 2001, 49, 887-892
4. Betulaceae
5. Jin, Z.-X.; Ito, H.; Yoshida, T. Phytochemistry 1998, 48, 333-338
6. Lee, M. W.; Tanaka, T.; Nonaka, G.; Nishioka, I. Phytochemistry 1992, 31, 2835-2839
7. Ishimatsu, M.; Tanaka, T.; Nonaka, G.; Nishioka, I. Phytochemistry 1989, 28, 3179-3184
8. Casuarinaceae
9. Okuda, T.; Yoshida, T.; Ashida, M.; Yazaki, K. Chem. Pharm. Bull. 1982, 30, 766-769
10. Okuda, T.; Yoshida, T.; Ashida, M.; Yazaki, K. J. Chem. Soc., Perkin Trans. 1 1983, 1765-1772
11. Coriariaceae: Hatano, T.; Hattori, S.; Okuda, T. Chem. Pharm. Bull. 1986, 34, 4533-4539
12. Elaeagnaceae
13. Ito, H.; Miki, K.; Yoshida, T. Chem. Pharm. Bull. 1999, 47, 536-542
14. Yoshida, T.; Tanaka, K.; Chen, X. M.; Okuda, T. Phytochemistry 1991, 30, 663-666
15. Yoshida, T.; Namba, O.; Kurokawa, K.; Amakura, Y.; Liu, Y.-Z.; Okuda, T. Chem. Pharm. Bull. 1994, 42, 2005-2010
16. Fagaceae: Feng, H.; Nonaka, G.; Nishioka, I. Phytochemistry 1988, 27, 1185-1189
17. Geraniaceae: Latte, K. P.; Kolodziej, H. Phytochemistry 2000, 54, 701-708
18. Juglandaceae: Tanaka, T.; Kouno, I. J. Nat. Prod. 1996, 59, 997-999
19. Melastomataceae
20. Yoshida, T.; Ito, H.; Hipolito, I. J. Phytochemistry 2005, 66, 1972-1983
21. Ling, S.-K.; Tanaka, T.; Kouno, I. J. Nat. Prod. 2002, 65, 131-135
22. Yoshida, T.; Nakata, F.; Hosotani, K.; Nitta, A.; Okuda, T. Phytochemistry 1992, 31, 2829-2833
23. Yoshida, T.; Haba, K.; Nakata, F.; Okano, Y.; Shingu, T.; Okuda, T. Chem. Pharm. Bull. 1992, 40, 66-71
24. Myrtaceae
25. El-shenawy, S. M.; Marzouk, M. S.; El Dib, R. A.; Abo Elyazed, H. E.; Shaffie, N. M.; Moharram, F. A. Rev. Latinoam. Quim. 2008, 36, 103-120
26. Yoshimura, M.; Ito, H.; Miyashita, K.; Hatano, T.; Taniguchi, S.; Amakura, Y.; Yoshida, T. Phytochemistry 2008, 69, 3062-3069
27. Shimoda, H.; Tanaka, J.; Kikuchi, M.; Fukuda, T.; Ito, H.; Hatano, T.; Yoshida, T. J. Agric. Food Chem. 2008, 56, 4444-4449
28. Fukuda, T.; Ito, H.; Yoshida, T. Phytochemistry 2003, 63, 795-801
29. Tanaka, T.; Orii, Y.; Nonaka, G.; Nishioka, I. Chem. Pharm. Bull. 1993, 41, 1232-1237
30. Maruyama, Y.; Matsuda, H.; Matsuda, R.; Kubo, M.; Hatano, T.; Okuda, T. Shoyakugaku Zasshi 1985, 39, 261-269
31. Punicaceae: Tanaka, T.; Nonaka, G.; Nishioka, I. Phytochemistry 1985, 24, 2075-2078
32. Rosaceae
33. Ochir, S.; Park, B. J.; Nishizawa, M.; Kanazawa, T.; Funaki, M.; Yamagishi, T. J. Nat. Med. 2010, 64, 383-387
34. Ito, H.; Nishitani, E.; Hatano, T.; Nakanishi, T.; Inada, A.; Murata, H.; Inatomi, Y.; Matsuura, N.; Ono, K.; Lang, F. A.; Murata, J.; Yoshida, T. Nat. Med. (Tokyo, Jpn.) 2001, 55, 218
35. Lin, J.-H.; Huang, Y.-F. Chin. Pharm. J. (Taipei, Taiwan) 1996, 48, 231-244
36. Hatano, T.; Ogawa, N.; Yasuhara, T.; Okuda, T. Chem. Pharm. Bull. 1990, 38, 3308-3313
37. Stachyuraceae
38. Hatano, T.; Yazaki, K.; Okonogi, A.; Okuda, T. Chem. Pharm. Bull. 1991, 39, 1689-1693
39. Part i of ref 3c.
40. Part ii of ref 3c.
41. Theaceae: Yagi, K.; Goto, K.; Nanjo, F. Chem. Pharm. Bull. 2009, 57, 1284-1288
42. Ku, K. M.; Choi, J. N.; Kim, J.; Kim, J. K.; Yoo, L. G.; Lee, S. J.; Hong, Y.-S.; Lee, C. H. J. Agric. Food Chem. 2010, 58, 418-426
43. Li, H.; Tanaka, T.; Zhang, Y.-J.; Yang, C.-R.; Kouno, I. Chem. Pharm. Bull. 2007, 55, 1325-1331
44. Dou, J.; Lee, V. S. Y.; Tzen, J. T. C.; Lee, M.-R. J. Agric. Food Chem. 2007, 55, 7462-7468
45. Nakai, M.; Fukui, Y.; Asami, S.; Toyoda-Ono, Y.; Iwashita, T.; Shibata, H.; Mitsunaga, T.; Hashimoto, F.; Kiso, Y. J. Agric. Food Chem. 2005, 53, 4593-4598
46. Niino, H.; Sakane, I.; Okanoya, K.; Kuribayashi, S.; Kinugasa, H. J. Agric. Food Chem. 2005, 53, 3995-3999
47. Maeda-Yamamoto, M.; Nagai, H.; Asai, K.; Moriwaki, S.; Horie, H.; Kohata, K.; Tachibana, H.; Miyase, T.; Sano, M. Food Sci. Technol. Res. 2004, 10, 186-190
48. Hashimoto, F.; Nonaka, G.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 1383-1389
49. Antiallergic: Tachibana, H.; Kubo, T.; Miyase, T.; Tanino, S.; Yoshimoto, M.; Sano, M.; Yamamoto-Maeda, M.; Yamada, K. Biochem. Biophys. Res. Commun. 2001, 280, 53-60
50. Antiviral: Saha, R. K.; Takahashi, T.; Kurebayashi, Y.; Fukushima, K.; Minami, A.; Kinbara, N.; Ichitani, M.; Sagesaka, Y. M.; Suzuki, T. Antiviral Res. 2010, 88, 10-18
51. Anti-HIV: Yoshida, T.; Ito, H.; Hatano, T.; Kurata, M.; Nakanishi, T.; Inada, A.; Murata, H.; Inatomi, Y.; Matsuura, N.; Ono, K.; Nakane, H.; Noda, M.; Lang, F. A.; Murata, J. Chem. Pharm. Bull. 1996, 44, 1436-1439
52. Antiinflammatory: Lee, C.-J.; Chen, L.-G.; Liang, W.-L.; Wang, C.-C. Food Chem. 2009, 118, 315-322
53. Antioxidant: Zhou, B.; Yang, Li.; Liu, Z.-L. Chem. Phys. Lipids 2004, 131, 15-25
54. Enhancement of other activities: Gondoin, A.; Grussu, D.; Stewart, D.; McDougall, G. J. Food Res. Int. 2010, 43, 1537-1544
55. Inhibition of enzymes: Toshima, A.; Matsui, T.; Noguchi, M.; Qiu, J.; Tamaya, K.; Miyata, Y.; Tanaka, T.; Tanaka, K. J. Sci. Food Agric. 2010, 90, 1545-1550
56. Immunostimulating activity: Monobe, M.; Ema, K.; Kato, F.; Maeda-Yamamoto, M. J. Agric. Food Chem. 2008, 56, 1423-1427
57. Khanbabaee, K.; Schulz, C.; Lötzerich, K. Tetrahedron Lett. 1997, 38, 1367-1368
58. Khanbabaee, K.; Lötzerich, K. Eur. J. Org. Chem. 1999, 3079-3083
59. Yamaguchi, S.; Ashikaga, Y.; Nishii, K.; Yamada, H. Org. Lett. 2012, 14, 5928-5931
60. Asakura, N.; Fujimoto, S.; Michihata, N.; Nishii, K.; Imagawa, H.; Yamada, H. J. Org. Chem. 2011, 76, 9711-9719
61. Pouységu, L.; Deffieux, D.; Malik, G.; Natangelo, A.; Quideau, S. Nat. Prod. Rep. 2011, 28, 853-874
62. Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742-1745
63. Dai, D.; Martin, O. R. J. Org. Chem. 1998, 63, 7628-7633
64. Zheng, S.; Laraia, L.; O'Connor, C. J.; Sorrell, D.; Tan, Y. S.; Xu, Z.; Venkitaraman, A. R.; Wu, W.; Spring, D. R. Org. Biomol. Chem. 2012, 10, 2590-2593
65. Su, X.; Thomas, G. L.; Galloway, W. R. J. D.; Surry, D. S.; Spandl, R. J.; Spring, D. R. Synthesis 2009, 3880-3896
66. Kasai, Y.; Michihata, N.; Nishimura, H.; Hirokane, T.; Yamada, H. Angew. Chem., Int. Ed. 2012, 51, 8026-8029
67. Yamada, H.; Nagao, K.; Dokei, K.; Kasai, Y.; Michihata, N. J. Am. Chem. Soc. 2008, 130, 7566-7567
68. ElSohly, H. N.; Ma, G. E.; Turner, C. E.; ElSohly, M. A. J. Nat. Prod. 1984, 47, 445-452
69. Pearson, A. J.; Bruhn, P. R. J. Org. Chem. 1991, 56, 7092-7097
70. Crich, D.; Bowers, A. A. J. Org. Chem. 2006, 71, 3452-3463
71. Freeman, A. W.; Chrisstoffels, L. A. J.; Fréchet, J. M. J. J. Org. Chem. 2000, 65, 7612-7617
72. Wolfrom, M. L.; Juliano, B. O. J. Am. Chem. Soc. 1960, 82, 1673-1677
73. Garegg, P. J.; Kvarnström, I.; Niklasson, A.; Niklasson, G.; Svensson, S. C. T. J. Carbohydr. Chem. 1993, 12, 933-953
74. Methods in Carbohydrate Chemistry. Vol. 2: Reactions of Carbohydrates; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963.
75. Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091
76. Vic, G.; Hastings, J. J.; Howarth, O. W.; Crout, D. H. G. Tetrahedron: Asymmetry 1996, 7, 709-720
77. Contour, M.-O.; Defaye, J.; Little, M.; Wong, E. Carbohydr. Res. 1989, 193, 283-287
78. Das, S. K.; Roy, J.; Reddy, K. A.; Abbineni, C. Cabohydr. Res. 2003, 338, 2237-2240
79. Weng, S.-S.; Lin, Y.-D.; Chen, C.-T. Org. Lett. 2006, 8, 5633-5636
80. Sanhueza, C. A.; Dorta, R. L.; Vázquea, J. T. Tetrahedron: Asymmetry 2008, 19, 258-264
81. Jamoisa, F.; Gofficc, F. L.; Yvina, J. C.; Plusquellecb, D.; Ferriéres, V. Open Glycosci. 2008, 1, 19-24
82. Wang, H.; Su, F.; Zhou, L.; Chen, X.; Le, P. Bioorg. Med. Chem. Lett. 2009, 19, 2796-2800
83. Weng, S.-S. Tetrahedron Lett. 2009, 50, 6414-6417
84. Verduyn, R.; Douwes, M.; van der Klein, P. A. M.; Mösinger, E. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1993, 49, 7301-7316
85. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. 1978, 17, 569-583
86. Brussee, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319
87. Kashiwada, T.; Huang, L.; Ballas, L. M.; Jiang, J. B.; Janzen, W. P.; Lee, K.-H. J. Med. Chem. 1994, 37, 195-200
88. Garegg, P. J. Acc. Chem. Res. 1992, 25, 575-580
89. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753
90. Fukase, K.; Hasuoka, A.; Kinoshita, I.; Aoki, Y.; Kusumoto, S. Tetrahedron 1995, 51, 4923-4932
91. Motawia, M. S.; Marcussen, J.; Moeller, B. L. J. Carbohydr. Chem. 1995, 14, 1279-1294
92. Lönn, H. Carbohydr. Res. 1985, 139, 105-113
93. Fukase, K.; Kinoshita, I.; Kanoh, T.; Nakai, Y.; Hasuoka, A.; Kusumoto, S. Tetrahedron 1996, 52, 3897-3904
94. Darko, D. Synlett 2000, 4, 544-546
95. Dasgupta, S.; Roy, B.; Mukhopadhyay, B. Carbohydr. Res. 2006, 341, 2708-2713
96. Duynstee, H. I.; de Koning, M. C.; Ovaa, H.; van der Marel, G. A.; van Boom, J. H. Eur. J. Org. Chem. 1999, 2623-2632
97. Mydock, L. K.; Demchenko, A. V. Org. Lett. 2008, 10, 2103-2106
98. Jensen, H. H.; Nordstrøm, L. U.; Bols, M. J. Am. Chem. Soc. 2004, 126, 9205-9213
99. Ren, Y.; Himmeldirk, K.; Chen, X. J. Med. Chem. 2006, 49, 2829-2837
100. Bols, M.; Hansen, H. C. Acta Chem. Scand. 1993, 47, 818-822
101. Binkely, R. C.; Ziepfel, J. C.; Himmeldirk, K. B. Carbohydr. Res. 2009, 344, 237-239
102. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. 1978, 17, 522-524
103. Boons, G.-J., Ed. In Carbohydrate Chemistry; Blackie Academic and Professional, Thomson Science: London, 1998; pp 21-25 and 108-110.
104. Yoshida, T.; Tanaka, K.; Chen, X.-M.; Okuda, T. Phytochemistry 1989, 28, 2451-2454
105. van Seteijin, A. M. P.; Kamerling, J. P.; Viegenthart, F. G. Carbohydr. Res. 1992, 225, 229-245